WO2024110891A1 - Pesticidal composition for seed treatment - Google Patents

Pesticidal composition for seed treatment Download PDF

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Publication number
WO2024110891A1
WO2024110891A1 PCT/IB2023/061791 IB2023061791W WO2024110891A1 WO 2024110891 A1 WO2024110891 A1 WO 2024110891A1 IB 2023061791 W IB2023061791 W IB 2023061791W WO 2024110891 A1 WO2024110891 A1 WO 2024110891A1
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composition
present
weight
range
pesticidal composition
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PCT/IB2023/061791
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French (fr)
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Sahila Sethi
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Sidhivinayak Chemtech Private Limited
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/04—Insecticides

Definitions

  • the present invention relates to synergistic pesticidal compositions for seed treatment and process of preparation thereof. More particularly, the present invention relates to a synergistic seed treatment composition comprising of fungicides and insecticides, capable of protecting plant propagation materials such as seeds, seedlings and plants/crops from harmful effects of seed-borne, soil borne pathogenic fungi and/or insect pests.
  • the present invention relates to synergistic pesticidal composition for seed treatment comprising (A) compound of Formula I, chemically known as 3-(difhioromethyl)-l-methyl-N-(3',4',5'- trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives; and (B) Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives and (C) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, esters or derivatives.
  • A compound of Formula I, chemically known as 3-(difhioromethyl)-l-methyl-N-(3',4',5'- trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives
  • B
  • Combination of insecticides and fungicides are used to broaden the control spectrum of insects and fungal pests in reduced dosage, thereby lowering environmental impact, and reduced the likelihood of resistance development.
  • Seed damage from insects and fungal pests is another major concern for agriculturalist/farmers.
  • diseases such as seed rot, powdery mildew etc. which reduces germination rates and significantly reduce yields.
  • Treating crops with combination of insecticides and fungicides helps reduce the damage caused by soil pests.
  • the control of phytopathogenic fungi along with insects is of great economic importance since fungal growth and insect pests on plants or on parts of plants retards foliage, fruit or seed production, and the overall quality and yield of a cultivated crop.
  • Another advantage of treating plant propagation materials including seeds is that higher yields can be obtained by improving germination rates, increasing the plant stand count, improved plant health.
  • seed treatment generally refers to application of a material to a seed prior to or during the time it is planted in soil to improve the handling characteristics of the seed, protect the seed prior to germination, support the germination and/or support the growth of the resulting plant. Seed treatment is the application of a pesticidal formulation prior to planting in order to provide protection and improve the establishment of healthy crops.
  • Seed treatment helps in ensuring optimal emergence during early development so that a crop has the best chance of reaching its genetic yield potential. Seed treatments eliminate the need for farmers to spray throughout the early stages of plant development, saving them time and money. Plant protection solutions can be used more efficiently by applying them to seeds, rather than spraying the field or crop, resulting in at least 95% reduction in chemical consumption and a lower environmental impact. Having "stronger" seeds means that more seeds produce healthy plants. In addition, some seed treatments also improve planting characteristics, handling and flowability. Seed treatments can often improve yield and quality and produce a solid return on investment. The benefits of seed treatment include amongst many benefits such as: increased germination, ensures uniform seedling emergence, protect seeds or seedlings from early season diseases and insect pests, improving crop emergence and its growth, improved plant population and thus higher productivity.
  • Seed treatment compositions must meet a number of special requirements, including their applicability to seeds in commercial equipment, the adhesion of the active ingredients to the treated seeds, and good flowability of the treated seeds, as an alternative to traditional broadcast spraying of pesticides. Importantly, the treated seeds must still be able to germinate.
  • a further problem arising with the use of pesticides is that the repeated and exclusive application of an individual compound pesticide often leads to a rapid selection of harmful target organism which has developed natural or adapted resistance against the active compound pesticide in question. Normally, such pests are also cross-resistant against other active ingredients having the same mode of action. An effective control of the pathogens with said active compounds is then not possible anymore.
  • the active ingredients of different mechanisms of action can be complex, some of the diseases are resistant to commonly used methods, and applications are based on the actual production of the effect.
  • the pesticide actives are used in the form of a dilute aqueous composition because it can attain a good interaction with the target organism, such as plants, fungi and insects.
  • target organism such as plants, fungi and insects.
  • active pesticide compounds that are used as pesticides are only sparingly or even insoluble in water.
  • the low solubility of such compounds present the challenges and difficulties to formulator in formulating pesticide compounds in stable flowable concentrate formulations that can be easily stored for a long time and which still have a high stability and effective activity until end use.
  • the FS (Flowable concentrate for seed treatment) formulations are a modification of suspension concentrates (SC) with supplemental additives for adhesion to the seed surface.
  • Typical problems with existing seed treatment solutions are arising as variable control level of seed borne and soil borne diseases in different crops particularly collar rot and dry rot in groundnut and other legume crops.
  • seed treatment chemical compositions in the art could be effective but unable to give prolonged protection to seeds and seedlings as well as growing plants from seed borne and soil borne diseases and insect pests.
  • certain active ingredients can protect seeds and seedlings considerably longer when applied at the higher dose but increased dose rate would cause adverse impact on beneficial soil microorganism, particularly, rhizobium spp. in legume crops, which are responsible for nitrogen fixation and to improve soil fertility.
  • Seed treatment formulations usually contain multiple active ingredients and/or high loading levels. Additionally, the active ingredient has to be accurately and evenly spread over the seed surface and must remain there throughout storage, drilling and while the seed starts to germinate. To successfully develop these types of formulations, superior formulation additives including surfactants/dispersants used in the formulation and the particle size of the formulation are essential.
  • superior formulation additives including surfactants/dispersants used in the formulation and the particle size of the formulation are essential.
  • the high performance requirement and complexity of seed treatment means formulating is the focal challenge.
  • insecticide and fungicide known in the art for the control of soil borne pests. However, these pesticidal compositions for seed treatment have issues in respect of lack of broad spectrum pest control, ineffective pesticidal control, ineffective germination rates, decreased stability, decreased plant/crop yield and phytotoxicity apart from stability issues.
  • CN107535503 discloses a pesticidal composition containing fluoxazole amide and neonicotinoids, and an auxiliary agent, wherein the neonicotinoid is any one of thiamethoxam, imidacloprid, acetamiprid, pymetrozine, dinotefuran and clothianidin, and the weight ratio of the active fluoxazole amide to the neonicotinoids is 1 : 80-80: 1.
  • CN107006480A discloses a bactericidal composition
  • a bactericidal composition comprising Fluorine containing compound as first active ingredient, a second active ingredient strobilurin fungicide, i.e. pyraclostrobin, azoxystrobin, kresoxim-methyl, trifloxystrobin and picoxystrobin and excipients, wherein the weight ratio of the first active ingredient to the second active ingredient is (1:40): (40:1), and the sum of the content is 1-90% of total weight of the composition.
  • a second active ingredient strobilurin fungicide i.e. pyraclostrobin, azoxystrobin, kresoxim-methyl, trifloxystrobin and picoxystrobin and excipients
  • the weight ratio of the first active ingredient to the second active ingredient is (1:40): (40:1), and the sum of the content is 1-90% of total weight of the composition.
  • pesticidal seed treatment composition comprising compound of Formula I, chemically known as 3 -(difluoromethyl)- 1- methyl-N-(3',4',5'-trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives when combined with Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives and at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, esters or derivatives overcame the aforementioned problems of the prior art compositions.
  • compound of Formula I chemically known as 3 -(difluoromethyl)- 1- methyl-N-(3',4',5'-trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives when combined with Trifloxystro
  • composition of present invention achieves a synergistic effect which extends the range of action of the components in the composition in two ways. Firstly, the rates of application of the components in the final composition are lowered whilst the action remains equally good. Secondly, the composition with an active ingredient combination still achieves a high degree of pest control even where the two individual components have become totally ineffective in such a low application rate range. This allows, on the one hand, a substantial broadening of the spectrum of pests that can be controlled and, on the other hand, increased safety in use.
  • the present invention further relates to a seed treatment composition having synergistically enhanced action of improving the health of plants, improved germination rate, synergistic control of pests with superior control efficiency and stability of the formulation. Additionally, the present invention also comprises a method for protection of plant propagation material from various fungi, fungal disease and insect pests comprising contacting the plant propagation materials with the seed treatment composition of present invention. Embodiments of the present invention may therefore ameliorate one or more of the above- mentioned problems. The present invention satisfies the existing needs, as well as others, and generally overcomes the deficiencies found in the prior art.
  • the present invention composition is synergistic, efficacious, environmentally friendly, simple to formulate, stable and safe to use.
  • Yet another objective of the present invention is to provide a novel and synergistic pesticidal composition for seed treatment that is stable, does not sediment upon storage and avoids hetero flocculation.
  • Yet another objective of the present invention is to provide a novel and stable synergistic pesticidal composition for seed treatment with a particle size of D90 i.e. less than 5 microns.
  • FS flowable concentrate
  • It is another objective of the present invention is to provide a novel and effective synergistic pesticidal composition for seed treatment that protects crop and the environmental damage.
  • It is another objective of the present invention is to provide a novel and effective synergistic pesticidal composition for seed treatment that is safe for environmental, has broad spectrum bioefficacy, longer residual efficacy and has no phytotoxicity.
  • Yet another objective of the present invention is to provide a novel and effective synergistic pesticidal composition for seed treatment that promotes plant health and improves crop yield. Furthermore, another objective of the present invention is to provide a novel and effective synergistic pesticidal composition for seed treatment which has a phytotonic effect, which results in improved grain size and yield; and has improved stability.
  • FS Flowable concentrate
  • It is another objective of the present invention to provide a synergistic pesticidal composition for seed treatment comprising (A) compound of Formula I, chemically known as 3-(difluoromethyl)- l-methyl-N-(3',4',5'-trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives and (B) Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives; and (C) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, esters or derivatives.
  • A compound of Formula I, chemically known as 3-(difluoromethyl)- l-methyl-N-(3',4',5'-trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters
  • composition of the present invention provides at least the following advantages: 1. Effective in protecting a wide range of crops, including fruits, vegetables, legumes, sugar crops, cereals, flowers, oil-seeds etc against major plant soil and seed borne pests.
  • the present invention relates to a novel and synergistic pesticidal composition for seed treatment that provides effective and simultaneous control of seed, soil borne insects and fungal diseases in variety of agricultural crops.
  • an aspect of the present invention provides a synergistic pesticidal composition for seed treatment, comprising (A) compound of Formula I, chemically known as 3- (difhioromethyl)-l-methyl-N-(3',4',5'-trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives and (B) Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives; and (C) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, esters or derivatives.
  • A compound of Formula I, chemically known as 3- (difhioromethyl)-l-methyl-N-(3',4',5'-trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivative
  • the present invention relates to synergistic pesticidal composition
  • synergistic pesticidal composition comprising (A) compound of Formula I, chemically known as 3-(difluoromethyl)-l-methyl-N-(3',4',5'- trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives, in the range of 1 to 20% by weight of the composition; and (B) Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives, in the range of 0.1 to 10% by weight of the composition; and (C) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, esters or derivatives, in the range of 10 to 50% by weight of the composition.
  • the present invention relates to stable synergistic pesticidal composition
  • stable synergistic pesticidal composition comprising
  • the pesticidal composition comprises of:
  • the pesticidal composition comprises of:
  • the stable synergistic pesticidal composition for seed treatment comprises particle size of D90, which is less than 5 microns.
  • the weight % of compound of Formula I fungicide, in the composition of present invention is preferably 6.66% by weight of the composition.
  • the weight % of Trifloxystrobin, in the composition of present invention is preferably 4% by weight of the composition.
  • the weight % of neonicotinoid insecticide in the composition of present invention is preferably 25% by weight of the composition.
  • formulation of the present synergistic pesticidal composition for seed treatment is Flowable Slurry or Flowable Concentrate (FS).
  • the flowable concentrate formulation or FS formulation for seed treatment having particle size of less than 5 microns.
  • a process for preparation of the synergistic pesticidal composition for seed treatment comprising:
  • the present synergistic pesticidal composition provides enhanced pest control after sowing and thus improved seedling germination rate.
  • the synergistic pesticidal composition for seed treatment is effective in controlling various pests including insect pests and fungal disease in various crops and plants including ground nut and cotton, sorghum, wheat, soybean, chilli, okra, maize, sunflower, tomato, rice (paddy), mango, apple, onion, cucumber, mustard, brinjal, tea, potato, citrus fruits, cumin, sugarcane.
  • the present invention provides a method of controlling or preventing pathogenic damage or pest damage in a plant propagation material, a plant, parts of a plant and/or plant organs that grow at a later point in time, which comprises applying on the plant propagation material a composition comprising abovementioned actives/ components .
  • active ingredient refers to that component of the composition responsible for control of pest.
  • Bioactive amounts as mentioned herein means that amount which, when applied to plant propagation material for seed treatment, is sufficient to give effect in such treatment.
  • control means to inhibit the ability of pests to survive, grow, feed and/or reproduce, or to limit the pests related damage or loss in plant propagation material including seeds, seedlings and crop plants.
  • the term “health of a plant” or “plant health” is defined as a condition of the plant and/or its products. As a result of the improved health; yield, plant vigour, quality and tolerance to abiotic or biotic stress is increased. As a result, the health of a plant is increased even in the absence of pest pressure. Accordingly, in an especially preferred embodiment according to the invention, the health of a plant is increased both in the presence and absence of biotic or abiotic stress factors.
  • plant propagation material is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil. These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
  • the term propagation material denotes seeds.
  • This invention relates to compositions for protecting plants, e.g., seeds of such economically important crops.
  • the invention furthermore relates to plant-protecting composition having synergistically enhanced action and to a method of improving the health of plants by applying said composition to the plants or the locus thereof, for example a plant or a plant propagation material, that is infested or liable to be infested by fungi and insect pests.
  • composition of present invention has the special advantage of being highly active against diseases in the soil that mostly occur in the early stages of plant development.
  • the yield of the treated plants is significantly improved.
  • the yield of the plants treated according to the method of the invention is increased synergistically.
  • the compound of Formula I of present invention (chemically known as 3 -(difluoromethyl)- 1- methyl-N-(3',4',5'-trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide) is a broad-spectrum carboxamide fungicide, used on a large variety of commercial crops. It stunts fungus growth by inhibiting the SQR enzyme.
  • the application of Formula I compound on crops, plants and plant propagation materials interferes with a number of key fungal life functions, including spore germination, germ tube growth and mycelium growth. This compound has been found to show specific efficacy against diseases such as seedling disease, sheath blight, black point, Botrytis gray mold, early blight and powdery mildew.
  • the chemical structure of compound Formula I is provided below:
  • the compound i.e. 3-(difluoromethyl)-l-methyl-N-(3',4',5'-trifluorobiphenyl-2-yl)-lH-pyrazole- 4-carboxamide shall be referred to as compound of Formula I in the entire specification and shall be meant to refer to this compound which has the IUPAC name and structure as mentioned herein above.
  • Trifloxystrobin has shown to have better fungal pest control in comparison to other strobilurin fungicides.
  • Trifloxystrobin has IUPAC name: methyl (2E)-(methoxyimino)(2- ⁇ [( ⁇ ( 1 E)- 1 - [3 - (trifluoromethyl)phenyl]ethylidene ⁇ amino)oxy]methyl ⁇ phenyl)acetate, which belongs to Oximino -acetate class and is classified as Qol-(quinone Outside inhibition) fungicide.
  • Trifloxystrobin is a widely used fungicide. It has a low aqueous solubility, a low volatility and, based on its chemical properties, it would not normally be expected to leach to groundwater.
  • Trifloxystrobin is represented by the following chemical structure:
  • Neonicotinoid insecticides being broad spectrum insecticides are a class of neuro-active insecticides chemically similar to nicotine.
  • Neonicotinoids are neurotoxins that target the nicotinic acetylcholine receptor acting as agonists.
  • Neonicotinoids also affects the CNS (central nervous system) of the insects as it binds agonistically to the post-synaptic nicotinic acetylcholine receptors that results in the spontaneous discharge of nerve impulses and eventual failure of the neuron to propagate any signal. Although they are effective as contact insecticides, it is the ability of these chemicals to translocate from the soil into leaves as systemic insecticides that has been one of the primary reasons for their popularity.
  • Neonicotinoids are used to protect a variety of vegetables, fruits, and major crops like corn, cotton, potato, rice, etc. against sucking insects like aphids, whiteflies, thrips, leaf- and plant hoppers.
  • these neonicotinoid insecticides Thiamethoxam and/or Clothianidin has been shown to have better insecticidal efficacy.
  • Thiamethoxam is chemically known as 3-[(2-chloro-l,3-thiazol-5-yl)methyl]-5-methyl-N-nitro- l,3,5-oxadiazinan-4-imine. It has the chemical structure as below:
  • Thiamethoxam is effective against aphids, thrips, beetles, centipedes, millipedes, sawflies, leaf miners, stem borers and termites.
  • Thiamethoxam is mainly used for control against sucking and chewing insects in vegetables, ornamentals, field crops, deciduous fruits, citrus, cotton and rice. It possesses contact and stomach activity. Its systemic properties have resulted in its use against foliar feeding insects via seed treatment, soil application or through irrigation systems. It is also registered for direct foliar application. Clothianidin was first disclosed in EP0375907.
  • Clothianidin is known as (E)-l-(2- chloro-l,3-thiazol-5-ylmethyl)-3-methyl-2-nitroguanidine (CAS REG No. 210880-92-5). Chemical structure of Clothianidin is as below:
  • Clothianidin is even effective for control of Diptera, Coleoptera and Lepidoptera pests and can be applied by a wide variety of treatment methods.
  • Clothianidin controls sucking and some chewing insects, such as aphids, thrips, and beetles.
  • Clothianidin may be applied to plant leaves, soil, or seeds.
  • a synergistic pesticidal composition for seed treatment comprises (A) compound of Formula I, chemically known as 3- (difhioromethyl)-l-methyl-N-(3',4',5'-trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives; and (B) Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives; and (C) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, esters or derivatives.
  • the synergistic pesticidal composition for seed treatment comprises (A) compound of Formula I, chemically known as 3-(difluoromethyl)- l-methyl-N-(3',4',5'-trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives , in the range of 1 to 20% by weight of the composition; and (B) Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives in the range of 0.1 to 10% by weight of the composition; and (C) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, in the range of 10 to 50% by weight of the composition.
  • A compound of Formula I, chemically known as 3-(difluoromethyl)- l-methyl-N-(3',4',5'-trifluorobiphenyl-2-yl)-l
  • the composition is useful for effectively controlling the soil borne and/or seed pests, improve the germination rate and also enhances the vigor/yield of the plant.
  • the synergistic composition of the present invention is particularly suited for the treatment of plant propagation materials, so that materials like seeds has a degree of protection during its germination and growth.
  • the present invention includes within its scope, all possible salts, esters and derivatives of the active ingredients of the composition.
  • the seed treatment application of the present synergistic composition may be carried out, e.g. by spraying, foaming, dusting or otherwise covering the seeds before sowing of the seeds and/or before emergence of the plants.
  • the present invention discloses a seed treatment composition which may be formulated as a Flowable concentrate (FS).
  • FS Flowable concentrates
  • This formulation is currently most popular type of seed treatment as it is water based and safer to apply. Also, since it is a liquid formulation, there are no dust problems and also provided easy clean up post-treatment machinery which is used for broadcasting.
  • the present invention provides a method of protecting a plant propagation material, a plant, parts of a plant and/or plant organs that grow at a later point in time against pathogenic damage or pest damage by applying to the plant propagation material a composition of the present invention.
  • the synergistic pesticidal composition further comprises agrochemically acceptable excipients which are selected from the group comprising of surfactants/dispersing agents, wetting agents , anti-foaming agents, anti-freezing agent, adjuvants, fillers, biocides/anti-microbial agent, thickeners, thickening agents, polymers, colorants, solvents, binders/structuring agents, thickener, buffering agent, fillers, quick coating agent or sticking agents, stabilizers, preservatives, adjuvants and solvents or a combination thereof.
  • agrochemically acceptable excipients which are selected from the group comprising of surfactants/dispersing agents, wetting agents , anti-foaming agents, anti-freezing agent, adjuvants, fillers, biocides/anti-microbial agent, thickeners, thickening agents, polymers, colorants, solvents, binders/structuring agents, thickener, buffering agent, fillers, quick coating agent or sticking agents,
  • the pesticidal composition controls various pests in field crops, vegetables, oil seed and pulses, horticulture etc.
  • suitable targets for seed treatment are various crop seeds, fruit species, vegetables, spices and ornamental seed, cereals, for example corn/maize (sweet and field), durum wheat, bengal gram, soybean, Groundnut, wheat, barley, oats, rye, triticale, bananas, rice, cotton, sunflower, potatoes, pasture, alfalfa, grasses, turf, sorghum, rapeseed, Brassica spp., sugar beet, egg-plants, tomato, lettuce, iceberg lettuce, pepper, cucumber, squash, melon, bean, dry-beans, peas, leek, garlic, onion, cabbage, carrot, tuber such as sugar cane, tobacco, coffee, turf and forage, cruciferous, cucurbits, grapevines, pepper, fodder beet, oil seed rape, pansy, impatiens, petunia and geranium.
  • corn/maize sweet and field
  • durum wheat bengal gram
  • soybean Groundnut
  • compositions of the present invention provide control of diseases caused by a broad spectrum of fungal plant pathogens in the Basidiomycete, Ascomycete, Oomycete and Deuteromycete classes.
  • the synergistic composition of the present invention are effective against phytopathogenic fungi, especially occurring in plants, including seed borne fungi and belong to the following classes such as those selected from Ascomycetes (e.g. Penicillium, Gaeumannomyces graminis); Basidiomycetes (e.g. the genus Hemileia, Rhizoctonia, Puccinia); Fungi imperfecti (e. g.
  • Botrytis Helminthosporium, Rhynchosporium, Fusarium, Septoria, Cercospora, Alternaria, Pyricularia and Pseudocercosporella herpotrichoides); Oomycetes (e. g. Phytophthora, Peronospora, Bremia, Pythium, Plasmopara); Zygomycetes (e.g., Rhizopus spp.).
  • the combination of the present invention is especially effective against Alternaria spp., Ascochyta spp., Aspergillus spp., Claviceps purpurea, Cochliobolus spp., Colletotrichum spp., Diplodia maydis, Erysiphe graminis, Fusarium spp.
  • the present composition may be used to control insect pests such as insects pests from the following orders: Lepidoptera, for example Agrotis ypsilon, Anticarsia gemmatalis, Chilo partellus, Cnaphalocrosis medinalis, Cydia pomonella, Pythium Diaphania nitidalis, , Earias insulana, Elasmopalpus lignosellus, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hyphantria cunea, Hyponomeuta malinellus, Leucoptera coffeella, Leucoptera scitella, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris bra
  • Dichromothrips corbetti Dichromothrips ssp , Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Scirtothrips dorsalis, Thrips oryzae, Thrips palmi and Thrips tabac;, termites (Isoptera), e.g.
  • Calotermes flavicollis Calotermes flavicollis, Coptotermes formosanus, Heterotermes aureus, Leucotermes flavipes, Microtermes spp., Odontotermes, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus and Termes natalensis; true bugs (Hemiptera), e.g.
  • Acrostemum hilare Amrasca biguttula biguttula, Amrasca devastans, Blissus leucopterus, Dysdercus cingulatus, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridu-la, Piesma quadrata, Solubea insularis , Thyanta perditor, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis crassivora, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrtho-s
  • Atta cephalotes Atta capiguara, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Monomorium pha-raonis, Solenopsis geminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xyloni, Pogonomyrmex barbatus, Pogonomyrmex califomicus, Pheidole megacephala, Dasy-mutilla occidentalis, Bombus spp.
  • Vespula squamosa Paravespula vulgaris, Paraves-pula pennsylvanica, Paravespula germanica, Dolichovespula maculata, Vespa crabro, Polistes rubiginosa, Camponotus floridanus, and Linepithema humile, crickets, grasshoppers, locusts (Orthoptera), e.g.
  • composition of present invention is suitable for controlling against many phytophagous insects’ pest’s including; Aphids, Jassid, Thrips, white fly, Mites (including termites), Mealybugs, Scales, Leaf miner, Gall midges, shootfly, stemfly, stemborer, root borer, fruit borer and other sucking pests.
  • pests including; Aphids, Jassid, Thrips, white fly, Mites (including termites), Mealybugs, Scales, Leaf miner, Gall midges, shootfly, stemfly, stemborer, root borer, fruit borer and other sucking pests.
  • the yield of the treated plant is increased.
  • the pesticidal composition is formulated as Flowable concentrate for seed treatment (FS).
  • the invention further provides the process for preparation of the said composition wherein, the preferred composition is Flowable concentrate for seed treatment (FS).
  • FS Flowable concentrate for seed treatment
  • synergistic seed treatment composition that is non-phytotoxic and has good stability.
  • the said composition is used to controls seed and soil borne fungal diseases like damping off, root rot, stem rot, pre emergence and post emergence seedling rot and blight caused by Pythium, Phytophthora, Rhizoctonia, Fusarium, Sclerotium, Aspergillus, Verticillium, Puccinia, Ustilago, Alternaria, Cercospora, Penicillium, Macrophomina, fungus.
  • the synergistic composition of the present invention is also useful in controlling soil insects like termites and also gives protection to crop after germination against various insects. Seed treatment can be applied to all types of seeds, including those from which plants genetically transformed to express specialized traits will germinate.
  • seed treatments with the composition of present invention can further enhance the ability of a plant to better withstand stressful growing conditions. This results in a healthier, more vigorous plant, which can lead to higher yields at harvest time.
  • Seed treatment with the synergistic composition of present invention are planted, the said composition protects the plants that grow after germination of the seed from damage by pests, and thus improves the growth characteristics of the plant through improved control of pests.
  • the present disclosure includes a method of protecting plants that grow at a later point in time against damage by pests, which method comprises treating seeds with composition comprising (A) compound of Formula I, chemically known as 3 -(difluoromethyl)- 1 -methyl -N- (3',4',5'-trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives and (B) Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives; and (C) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, esters or derivatives.
  • composition comprising (A) compound of Formula I, chemically known as 3 -(difluoromethyl)- 1 -methyl -N- (3',4',5'-trifluorobiphenyl-2-yl)-lH-pyrazole-4
  • the present disclosure also contemplates the treatment of other plant propagation materials.
  • the descriptions herein involving seed treatment are also intended to apply equally well to methods, compositions and materials involving the treatment of other plant propagation material with the synergistic composition of present invention.
  • the seed treatment can be applied as a thin film (such as a dressing) of the formulation including the active ingredient on a seed, where the original size and/or shape of the seed are recognizable; or as a thick film (such as a coating or pelleting) with many layers of the same or different materials where the original shape and/or size of the seed is no longer recognizable.
  • agrochemically acceptable excipients used in the present invention includes but not limited to the group comprising dispersing agent, wetting agent, anti-foaming agent, anti-freezing agent, adjuvants, fillers, antimicrobial/anti-bacterial agent, thickening agent/thickeners, colouring agents, pigments, dyes and solvents or mixtures thereof. Additional components may also be added to present compositions e.g., protective colloids, adhesives, thixotropic agents, penetration agents, stabilisers, quick coating agents, spreaders, binders, anti-caking agents, stickers.
  • dispersing agent used herein examples include but not limited to polyaryl phenyl ether phosphate, tristyryl phenol ethylated, acrylic copolymer, ethoxylated tristryl phenol Sulphate, naphthalene sulfonic acid, sodium salt condensate with formaldehyde, ethoxylated oleyl cetyl alcohol, polyalkelene glycol ether, ethoxylated fatty alcohol , sodium polymethyl methacrylate, sodium polyacrylate, , sodium lignosulphonate, calcium lignosulphonate, alkylphenol polyoxyethylene ether, polycarboxylate, fatty alcohol polyoxyethylene ether, alcohol polyglycol ether or mixtures thereof and is present in the range of 0.5 -10% by weight of the composition.
  • wetting agents used herein include but not limited to tristyrylphenol ethoxylate nonionic emulsifier, mixture of non-ionic surfactants , alkoxylated alcohol, block copolymer, alcohol polyglycol ether, alkyl olefin sulphates, dioctyl sulpho succinate, alkyl naphthalene sulphate, alkyl phenol ethoxylates, tri-styrenated phenol ethoxylate, EO/PO block co-polymers, sodium lauryl sulphate, sodium ligno sulphates or mixtures thereof present in the range of 0.5- 10% by weight of the total composition.
  • antifoaming agent used herein examples include but not limited to silicon emulsion based anti-foam agents, Siloxane polyalkyleneoxide, Polydimethylsiloxane, trisiloxane ethoxylates, silicone oil, silicone compound, C10 ⁇ C20 saturated fat acid compounds or C8 ⁇ C10 aliphatic alcohols compound, vegetable oil based antifoam, tallow based fatty acids, polyalkyleneoxide modified polydimethylsiloxane or mixtures thereof and present in the range of 0.01-3% by weight of the total composition.
  • Anti-freezing agent used herein include but not limited to glycol, propylene glycol, mono ethylene glycol, glycerine, diethylene glycol, sorbitol, urea, mannitol, polyethylene glycol or mixtures thereof and present in the range of 0.1 -20% by weight of the total composition.
  • adjuvants used herein include but not limited to silicone ethoxylated oil, polyvinyl pyrrolidon, poly vinyl alcohol, blend of poly terpene resin or mixtures thereof and is present in the range of 0.1 - 10% by weight of the composition.
  • Fillers used herein include but not limited to silicon dioxide, china-clay, kaolin, starch, bentonite, precipitated silica, fumed silica, talcum powder, lactose, ammonium sulphate, sodium Sulphate, magnesium sulphate, sodium citrate, sodium chloride, potassium chloride or mixtures thereof and present in the range of 0.1-80% by weight of the composition.
  • anti-bacterial or anti-microbial agents used herein include but not limited to 1,2- benzisothiazolin-3-one, formaldehyde, sodium benzoate/Sodium o-phenylphenate, 5-chloro-2- methyl-4-isothiazolin-3-one & 2- methyl-4-isothiazolin-3-one, potassium sorbate or mixtures thereof and present in the range of 0.01-1% by weight of the composition.
  • Thickeners or thickening agents used herein include but not limited to polysaccharides, carboxymethyl cellulose, bentonite clay, aluminium magnesium silicate, hydroxy propyl cellulose, xanthan gum, gum arabic, gaur gum, carbomer, chitosan, precipitated silica or mixtures thereof and present in the range of 0.01- 3% by weight of the composition.
  • Colouring agent used herein includes dyes or pigments and present in the range of 0.1- 10% by weight of the composition.
  • solvents used herein include but not limited to heavy aromatic hydrocarbon, N methyl pyrollidone, Di methyl sulfoxide, N- alcohol, alkyl amide, vegetable oil, mineral oil, aromatic solvents, water. Any of the above mentioned solvent can be used either alone or in combination thereof and present in the range of 0.1-90% by weight of the composition.
  • quick coating agent or sticking agents include but not limited to polyesters, polyamides, poly- carbonates, polyurea and polyurethanes, acrylate polymers and copolymers, styrene copolymers, butadiene copolymers, polysaccharides such as starch and cellulose derivatives, vinylalcohol, vinylacetate and vinylpyrrolidone polymers and copolymers, polyethers, epoxy, phenolic and melamine resins, polyolefins and define copolymers or mixtures thereof.
  • acrylate polymers such as poly(methacrylate), poly(ethyl methacrylate), poly(methylmethacrylate), acrylate copoylmers and styrene-acrylic copolymers as defined herein below, poly(styrenecomaleic anhydride), cellulosic polymers such as ethyl cellulose, cellulose acetate, cellulose acetatebutyrate, acetylated mono, di, and triglycerides, poly(vinylpyrrolidone), vinyl acetate polymers and copolymers, poly(alkylene glycol), styrene butadiene copolymers, poly(orthoesters), alkyd resins, and mixtures of two or more of these.
  • acrylate polymers such as poly(methacrylate), poly(ethyl methacrylate), poly(methylmethacrylate), acrylate copoylmers and styrene-acrylic copolymers as
  • Biodegradable polymers that are biodegradable are also useful in the present invention.
  • a polymer is biodegradable if is not water soluble, but is degraded over a period of several weeks when placed in an application environment.
  • biodegradable polymers that are useful in the present invention include biodegradable polyesters, starch, polylactic acid starch blends, polylactic acid, poly(lactic acid-glycolic acid) copolymers, polydioxanone, cellulose esters, ethyl cellulose, cellulose acetate butyrate, starch esters, starch esteraliphatic polyester blends, modified corn starch, polycaprolactone, poly (namylmethacry late), wood rosin, polyanhydrides, polyvinylalcohol, polyhydroxybutyratevalerate, biodegradable aliphatic polyesters, and polyhydroxybutyrate or mixtures thereof.
  • spreaders used herein include but not limited to organosilicone surfactants, trisiloxane ethoxylate or mixtures thereof.
  • the kit-of-parts comprises an instructions manual, said instructions manual comprising instructions directing a user to admix the components before being used.
  • composition of the present invention can also comprise or may be applied together and/or sequentially with further active compounds.
  • further compounds can be selected from fertilizers or micronutrient donors or microorganisms or other preparations that influence plant growth, such as inoculants (e.g. a strain of nitrogen-fixing bacteria), and plant inducers.
  • a stable Flowable Concentrate/Slurry (FS) composition of present invention is provided.
  • synergistic action expected for a given combination of two active components can be calculated as follows:
  • synergistic action expected for a given combination of three active components can be calculated as follows:
  • E represents expected percentage of pesticidal control for the combination of the two or three active ingredients at defined doses (for example equal to x, y and z, respectively).
  • X is the percentage of pesticidal control observed by the compound (Fluxapyroxad/ Compound of Formula I ) at a defined dose (equal to x).
  • Y is the percentage of pesticidal control observed by the compound (Trifloxystrobin) at a defined dose (equal to y).
  • Z is the percentage of pesticidal control observed by the compound (Thiamethoxam or Clothianidin) at a defined dose (equal to z).
  • T2 Fluxapyroxad + Trifloxystrobin + Thiamethoxam FS (6.66%+4.0%+25%)
  • T3 Fluxapyroxad + Trifloxystrobin + Thiamethoxam FS (20%+10%+10%)
  • T4 Fluxapyroxad + Trifloxystrobin + Clothianidin FS (l%+0.1 %+50%)
  • Method of sowing Line sowing on flat beds.
  • Germination Percentage Counted number of seeds were sown in 10 sq m area in each plot are marked and germination percentage is calculated as given below
  • Collar rot (Aspergillus niger). Total no of infected were counted at 30 days after sowing in each plot and percentage collar rot control was calculated as
  • White Grub Damage is caused by grubs where, young grubs feed on fine rootlets while mature grubs feed on both roots and pods. The affected plants show varying degrees of wilting, which ultimately die and died plants can easily be pulled out. The grubs cause infestation in patches leading to ‘patchy appearance’ of field. For recording the observation for damage due to white grub total no of wilted/dead plants were counted at 30 days after sowing in each plant and percentage white grub control was calculated as
  • No. of pods per plant No. of pods per plants was recorded at the time of harvest. For recording the observation average of 10 plants from each plot were taken. Yield: Pods from each plot were recorded at harvest and converted into kg/ha.
  • composition of present invention is stable, synergistically efficacious in terms of disease control and improves the germination and yield of the crops.

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Abstract

The present invention relates to a synergistic pesticidal composition for seed treatment capable of protecting plant propagation materials such seeds, seedlings; and plants/crops from harmful effects of seed-borne, soil borne pathogenic fungi and/or insect pests.

Description

PESTICIDAL COMPOSITION FOR SEED TREATMENT
FIELD OF THE INVENTION
The present invention relates to synergistic pesticidal compositions for seed treatment and process of preparation thereof. More particularly, the present invention relates to a synergistic seed treatment composition comprising of fungicides and insecticides, capable of protecting plant propagation materials such as seeds, seedlings and plants/crops from harmful effects of seed-borne, soil borne pathogenic fungi and/or insect pests. Further and more particularly, the present invention relates to synergistic pesticidal composition for seed treatment comprising (A) compound of Formula I, chemically known as 3-(difhioromethyl)-l-methyl-N-(3',4',5'- trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives; and (B) Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives and (C) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, esters or derivatives.
BACKGROUND OF THE INVENTION
Combination of insecticides and fungicides are used to broaden the control spectrum of insects and fungal pests in reduced dosage, thereby lowering environmental impact, and reduced the likelihood of resistance development. Seed damage from insects and fungal pests is another major concern for agriculturalist/farmers. There are various diseases, such as seed rot, powdery mildew etc. which reduces germination rates and significantly reduce yields. Treating crops with combination of insecticides and fungicides helps reduce the damage caused by soil pests. The control of phytopathogenic fungi along with insects is of great economic importance since fungal growth and insect pests on plants or on parts of plants retards foliage, fruit or seed production, and the overall quality and yield of a cultivated crop.
Another advantage of treating plant propagation materials including seeds is that higher yields can be obtained by improving germination rates, increasing the plant stand count, improved plant health.
The term "seed treatment" generally refers to application of a material to a seed prior to or during the time it is planted in soil to improve the handling characteristics of the seed, protect the seed prior to germination, support the germination and/or support the growth of the resulting plant. Seed treatment is the application of a pesticidal formulation prior to planting in order to provide protection and improve the establishment of healthy crops.
Seed treatment helps in ensuring optimal emergence during early development so that a crop has the best chance of reaching its genetic yield potential. Seed treatments eliminate the need for farmers to spray throughout the early stages of plant development, saving them time and money. Plant protection solutions can be used more efficiently by applying them to seeds, rather than spraying the field or crop, resulting in at least 95% reduction in chemical consumption and a lower environmental impact. Having "stronger" seeds means that more seeds produce healthy plants. In addition, some seed treatments also improve planting characteristics, handling and flowability. Seed treatments can often improve yield and quality and produce a solid return on investment. The benefits of seed treatment include amongst many benefits such as: increased germination, ensures uniform seedling emergence, protect seeds or seedlings from early season diseases and insect pests, improving crop emergence and its growth, improved plant population and thus higher productivity.
One typical problem arising in the field of pest control lies in the need to reduce the dosage rates of the active ingredient in order to reduce or avoid unfavourable environmental or toxicological effects whilst still allow effective pest control. There also exists the need for pesticidal agents that combined with prolonged control, that are, fast action with long residual lasting action.
Another issue that farmers face is the rapid release of pesticides used for seed treatment in the soil or water. The release of pesticidal agents, particularly in seed treatment (e.g., seed soaking), is a major issue due to environmental safety on the one hand and the loss of pesticidal agent protection against soil-borne fungi and insects on the other. Seed treatment compositions must meet a number of special requirements, including their applicability to seeds in commercial equipment, the adhesion of the active ingredients to the treated seeds, and good flowability of the treated seeds, as an alternative to traditional broadcast spraying of pesticides. Importantly, the treated seeds must still be able to germinate. A further problem arising with the use of pesticides is that the repeated and exclusive application of an individual compound pesticide often leads to a rapid selection of harmful target organism which has developed natural or adapted resistance against the active compound pesticide in question. Normally, such pests are also cross-resistant against other active ingredients having the same mode of action. An effective control of the pathogens with said active compounds is then not possible anymore.
The active ingredients of different mechanisms of action can be complex, some of the diseases are resistant to commonly used methods, and applications are based on the actual production of the effect. There is a need in selecting different active ingredients/agrochemically active compounds which can manifest to improve control efficiency, reducing the use of pesticides, possess broad spectrum activity and improve the germination rate, yield and plant vigour, health and are non-phytotoxic. It is always preferable to be able to reduce the amount of chemical agents released into the environment while still ensuring effective pest and disease control. Although many pest control agent combinations have been studied, a high synergistic action has not always been found.
Thus, there is a need of a pesticidal composition for seed treatment which can overcome some of the aforementioned existing problems and can be prepared easily without much complex manufacturing process. There is also a need for a synergistic pesticidal composition for seed treatment that has broad spectrum pest control as well as provide desired bio-efficacy and is storage stable throughout its entire shelf life. However, the biological properties of combination of known compounds are not completely satisfactory in the field of pest control. There is a need for cost-effective composition while avoiding the health and safety concerns of the prior art.
Further, resistance has developed as a result of long-term use of single and/or binary active combinations. Commercially available seed treatment formulations containing fungicide, or insecticide have drawbacks such as hetero flocculation and sedimentation during storage, as well as stability issues and a time-consuming manufacturing process. Particle aggregation/coagulation occurs in the flowable concentrate formulations, making it difficult to dispense the product from the container, resulting in decreased stability and shelf life.
In general use, the pesticide actives are used in the form of a dilute aqueous composition because it can attain a good interaction with the target organism, such as plants, fungi and insects. However, most active pesticide compounds that are used as pesticides are only sparingly or even insoluble in water. The low solubility of such compounds present the challenges and difficulties to formulator in formulating pesticide compounds in stable flowable concentrate formulations that can be easily stored for a long time and which still have a high stability and effective activity until end use. The FS (Flowable concentrate for seed treatment) formulations are a modification of suspension concentrates (SC) with supplemental additives for adhesion to the seed surface.
Typical problems with existing seed treatment solutions are arising as variable control level of seed borne and soil borne diseases in different crops particularly collar rot and dry rot in groundnut and other legume crops. Alternately, seed treatment chemical compositions in the art could be effective but unable to give prolonged protection to seeds and seedlings as well as growing plants from seed borne and soil borne diseases and insect pests. However, certain active ingredients can protect seeds and seedlings considerably longer when applied at the higher dose but increased dose rate would cause adverse impact on beneficial soil microorganism, particularly, rhizobium spp. in legume crops, which are responsible for nitrogen fixation and to improve soil fertility.
There are certain limitations in formulating a seed treatment composition. Seed treatment formulations usually contain multiple active ingredients and/or high loading levels. Additionally, the active ingredient has to be accurately and evenly spread over the seed surface and must remain there throughout storage, drilling and while the seed starts to germinate. To successfully develop these types of formulations, superior formulation additives including surfactants/dispersants used in the formulation and the particle size of the formulation are essential. The high performance requirement and complexity of seed treatment means formulating is the focal challenge. There are many combinations of insecticide and fungicide known in the art for the control of soil borne pests. However, these pesticidal compositions for seed treatment have issues in respect of lack of broad spectrum pest control, ineffective pesticidal control, ineffective germination rates, decreased stability, decreased plant/crop yield and phytotoxicity apart from stability issues.
Reference may be made to IN223737 patent, which relates to active compound composition, comprising Trifloxystrobin and at least one compound selected from the group of insecticides consisting of compound of the formula (II), thiacloprid, acetamiprid, nitenpyram, thiamethoxam, clothianidin, dinotefuran, wherein the ratio of trifloxystrobin to one compound of formula II is from 1:0.1 to 1:10 and trifloxystrobin to others is 1:0.05 to 1: 20.
Reference may also be made to CN107535503, which discloses a pesticidal composition containing fluoxazole amide and neonicotinoids, and an auxiliary agent, wherein the neonicotinoid is any one of thiamethoxam, imidacloprid, acetamiprid, pymetrozine, dinotefuran and clothianidin, and the weight ratio of the active fluoxazole amide to the neonicotinoids is 1 : 80-80: 1.
Reference may further be made to CN107006480A, which discloses a bactericidal composition comprising Fluorine containing compound as first active ingredient, a second active ingredient strobilurin fungicide, i.e. pyraclostrobin, azoxystrobin, kresoxim-methyl, trifloxystrobin and picoxystrobin and excipients, wherein the weight ratio of the first active ingredient to the second active ingredient is (1:40): (40:1), and the sum of the content is 1-90% of total weight of the composition.
There is however a need for improvement of these combinations as single and binary active combinations used over a long period of time has resulted in resistance. Thus, there is a need for a synergistic pesticidal composition for seed treatment which exhibits broad spectrum control of pests and is storage stable during its entire shelf-life. Further, there is a need for a process comprising use of suitable adjuvants that can interfere with particle agglomeration providing a stable synergistic pesticidal composition which exhibits, fungicidal and insecticidal properties and has curative along with protective action. Therefore, there is still a need in the art for a ready to use flowable concentrate seed treatment composition comprising combination of fungicides and insecticide active compounds having advantageous activity profile, high stability and a synergistically improved action, which allows for reduced application rate in comparison with individual application of the active compounds and has no adverse effect on root nodulation rhizobium bacterium in legume crops.
During the research leading to present invention, it has been found that pesticidal seed treatment composition comprising compound of Formula I, chemically known as 3 -(difluoromethyl)- 1- methyl-N-(3',4',5'-trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives when combined with Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives and at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, esters or derivatives overcame the aforementioned problems of the prior art compositions.
It has now been found, surprisingly, that composition of present invention achieves a synergistic effect which extends the range of action of the components in the composition in two ways. Firstly, the rates of application of the components in the final composition are lowered whilst the action remains equally good. Secondly, the composition with an active ingredient combination still achieves a high degree of pest control even where the two individual components have become totally ineffective in such a low application rate range. This allows, on the one hand, a substantial broadening of the spectrum of pests that can be controlled and, on the other hand, increased safety in use.
The present invention further relates to a seed treatment composition having synergistically enhanced action of improving the health of plants, improved germination rate, synergistic control of pests with superior control efficiency and stability of the formulation. Additionally, the present invention also comprises a method for protection of plant propagation material from various fungi, fungal disease and insect pests comprising contacting the plant propagation materials with the seed treatment composition of present invention. Embodiments of the present invention may therefore ameliorate one or more of the above- mentioned problems. The present invention satisfies the existing needs, as well as others, and generally overcomes the deficiencies found in the prior art.
The present invention composition is synergistic, efficacious, environmentally friendly, simple to formulate, stable and safe to use.
OBJECTIVES AND ADVANTAGES OF THE INVENTION
It is a primary objective of the present invention to provide a novel, effective and synergistic pesticidal composition for treatment of plant propagation materials like seeds having high efficacy and high selectivity.
It is another objective of the present invention to provide improved pesticidal composition for seed treatment comprising combinations of fungicides and insecticide for broad spectrum control of pests.
It is another objective of the present invention to provide a novel process for preparing stable synergistic pesticidal composition for seed treatment.
Yet another objective of the present invention is to provide a novel and synergistic pesticidal composition for seed treatment that is stable, does not sediment upon storage and avoids hetero flocculation.
Yet another objective of the present invention is to provide a novel and stable synergistic pesticidal composition for seed treatment with a particle size of D90 i.e. less than 5 microns.
It is another objective of the present invention to provide a flowable concentrate (FS) formulation that allows moisture from soil to penetrate into the seed coating film.
It is another objective of the present invention to provide a novel and a stable synergistic pesticidal composition for controlling insect pests and fungal diseases. It is another objective of the present invention is to provide a novel and effective synergistic pesticidal composition for seed treatment that has both preventive and curative action in addition to phytotonic action; and is active against all life stages of major plant pathogens.
It is another objective of the present invention is to provide a novel and effective synergistic pesticidal composition for seed treatment that protects crop and the environmental damage.
It is another objective of the present invention to provide a novel and effective synergistic pesticidal composition for seed treatment that improves germination rate, increased plant stand count and plant health, which results in higher yields.
It is another objective of the present invention to provide a novel and effective synergistic pesticidal composition for seed treatment that improves quality and quantity of the targeted crops and plants.
It is another objective of the present invention to provide a novel and effective synergistic pesticidal composition for seed treatment that is ideal for pest resistance management and disease control.
It is another objective of the present invention is to provide a novel and effective synergistic pesticidal composition for seed treatment that is safe for environmental, has broad spectrum bioefficacy, longer residual efficacy and has no phytotoxicity.
It is another objective of the present invention to provide a novel and effective synergistic pesticidal composition for seed treatment that is stable over wide range temperatures and environmental changes.
It is another objective of the present invention to provide a novel and effective synergistic pesticidal composition for seed treatment with enhanced efficacy and penetration capacity.
Yet another objective of the present invention is to provide a novel and effective synergistic pesticidal composition for seed treatment that promotes plant health and improves crop yield. Furthermore, another objective of the present invention is to provide a novel and effective synergistic pesticidal composition for seed treatment which has a phytotonic effect, which results in improved grain size and yield; and has improved stability.
It is another objective of the present invention to provide an easy to formulate, novel and stable synergistic pesticidal composition for seed treatment.
It is another objective of the present invention to provide improved, stable and ready to use composition having synergistic and superior properties compared to prior art formulations or mixtures or compositions.
It is yet another objective of the present invention to provide a chemically stable synergistic seed treatment composition which is preferably formulated as a Flowable concentrate (FS).
It is yet another objective of the present invention to provide a novel, synergistic seed treatment composition which has a broad spectrum of activity, especially against insects and fungi.
It is another objective of the present invention to provide a synergistic pesticidal composition for seed treatment comprising (A) compound of Formula I, chemically known as 3-(difluoromethyl)- l-methyl-N-(3',4',5'-trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives and (B) Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives; and (C) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, esters or derivatives.
It is another objective of the present invention to provide a stable synergistic pesticidal composition that shows technical advancement over the existing pesticides or combination of pesticides.
Compared with the prior art, the composition of the present invention provides at least the following advantages: 1. Effective in protecting a wide range of crops, including fruits, vegetables, legumes, sugar crops, cereals, flowers, oil-seeds etc against major plant soil and seed borne pests.
2. Better control of soil and seed borne pests in a shorter period of time.
3. Improves germination rate, increased plant health, reduced risk of occupational hazard, lower cost of application, better cost-benefit ratio to the end user, reduced fuel and labour cost, time savings for the applicator, and reduced wear of equipment and loss caused by mechanical damage to the crop and soil.
4. Stable and prolonged shelf life of the composition.
5. Synergistic in terms of pest (disease and insect) control
6. Synergistic control in comparison with binary mixtures against collar rot (Aspergillus niger) and White grub, Anthracnose, Rhizoctonia root, rot, Cotyledonary spot, Seedling Disease, Powdery Mildew, Early blight, Septoria leaf spot, Purple blotch, Alternaria leaf, Tikka, Frog eye leaf spot, Jassids & White fly, Brown plant hopper, Aphids, Thrips, termites, Shoot fly, Stem Fly, Green leafhoppers, Early shootborer, Stem borer, Gall midge, Leaf, folder, White backed planthopper, Green leafhopper, Psylla.
SUMMARY OF THE INVENTION:
The present invention relates to a novel and synergistic pesticidal composition for seed treatment that provides effective and simultaneous control of seed, soil borne insects and fungal diseases in variety of agricultural crops.
Therefore, an aspect of the present invention provides a synergistic pesticidal composition for seed treatment, comprising (A) compound of Formula I, chemically known as 3- (difhioromethyl)-l-methyl-N-(3',4',5'-trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives and (B) Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives; and (C) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, esters or derivatives. More particular, the present invention relates to synergistic pesticidal composition comprising (A) compound of Formula I, chemically known as 3-(difluoromethyl)-l-methyl-N-(3',4',5'- trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives, in the range of 1 to 20% by weight of the composition; and (B) Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives, in the range of 0.1 to 10% by weight of the composition; and (C) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, esters or derivatives, in the range of 10 to 50% by weight of the composition.
More particular, the present invention relates to stable synergistic pesticidal composition comprising
(A) compound of Formula I, chemically known as 3-(difhioromethyl)-l-methyl-N-(3',4',5'- trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives, in the range of 1 to 20% by weight of the composition; and (B) Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives, in the range of 0.1 to 10% by weight of the composition; and (C) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, esters or derivatives, in the range of 10 to 50% by weight of the composition, wherein the particle size (D90) of the composition is less than 5 microns.
In one other aspect/embodiment of the present invention, the pesticidal composition comprises of:
(A) compound of Formula I, chemically known as 3-(difhioromethyl)-l-methyl-N-(3',4',5'- trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives, in the range of 1 to 20% by weight of the composition; and (B) Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives, in the range of 0.1 to 10% by weight of the composition; and (C) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, esters or derivatives, in the range of 10 to 50% by weight of the composition; and D) one or more agrochemically acceptable excipients In one another aspect/embodiment of the present invention, the pesticidal composition comprises of:
(A) compound of Formula I, chemically known as 3-(difhioromethyl)-l-methyl-N-(3',4',5'- trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives, in the range of 1 to 20% by weight of the composition; and (B) Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives, in the range of 0.1 to 10% by weight of the composition; and (C) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, esters or derivatives, in the range of 10 to 50% by weight of the composition; and D) one or more agrochemically acceptable excipients, wherein the particle size (D90) of the composition is less than 5 microns.
In another embodiment of the present invention, the stable synergistic pesticidal composition for seed treatment, comprises particle size of D90, which is less than 5 microns.
In yet another preferred embodiment of the present invention, the weight % of compound of Formula I fungicide, in the composition of present invention, is preferably 6.66% by weight of the composition.
In yet another preferred embodiment of the present invention, the weight % of Trifloxystrobin, in the composition of present invention, is preferably 4% by weight of the composition.
In yet another preferred embodiment of the present invention, the weight % of neonicotinoid insecticide in the composition of present invention, is preferably 25% by weight of the composition.
In one another preferred embodiment formulation of the present synergistic pesticidal composition for seed treatment is Flowable Slurry or Flowable Concentrate (FS).
In one another preferred embodiment of the present invention, the flowable concentrate formulation or FS formulation for seed treatment having particle size of less than 5 microns. In another embodiment of the present invention, it is provided a process for preparation of the synergistic pesticidal composition for seed treatment comprising:
(A) compound of Formula I, chemically known as 3-(difhioromethyl)-l-methyl-N-(3',4',5'- trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives, in the range of 1 to 20% by weight of the composition; and (B) Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives, in the range of 0.1 to 10% by weight of the composition; and (C) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, esters or derivatives, in the range of 10 to 50% by weight of the composition.
In another embodiment of the present invention, it is provided a process for preparation of the synergistic pesticidal composition for seed treatment comprising:
(A) compound of Formula I, chemically known as 3-(difhioromethyl)-l-methyl-N-(3',4',5'- trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives, in the range of 1 to 20% by weight of the composition; and (B) Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives, in the range of 0.1 to 10% by weight of the composition; and (C) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, esters or derivatives, in the range of 10 to 50% by weight of the composition; and D) one or more agrochemically acceptable excipients, wherein the particle size (D90) of the composition is less than 5 microns.
In an embodiment of the present invention, the present synergistic pesticidal composition provides enhanced pest control after sowing and thus improved seedling germination rate.
An another embodiment of the present invention, the synergistic pesticidal composition for seed treatment is effective in controlling various pests including insect pests and fungal disease in various crops and plants including ground nut and cotton, sorghum, wheat, soybean, chilli, okra, maize, sunflower, tomato, rice (paddy), mango, apple, onion, cucumber, mustard, brinjal, tea, potato, citrus fruits, cumin, sugarcane. Accordingly, in a further embodiment of the present invention, the present invention provides a method of controlling or preventing pathogenic damage or pest damage in a plant propagation material, a plant, parts of a plant and/or plant organs that grow at a later point in time, which comprises applying on the plant propagation material a composition comprising abovementioned actives/ components .
DETAILED DESCRIPTION OF THE INVENTION
Discussed below are some representative embodiments of the present invention. The invention in its broader aspects is not limited to the specific details and representative methods.
All technical and scientific terms used herein have the same meanings as commonly understood by someone ordinarily skilled in the art to which the present subject matter belongs.
The invention according to its various aspects is particularly pointed out and distinctly claimed in the appended claims read in view of this specification and appropriate equivalents.
The terminology used, in the present disclosure, is only for the purpose of explaining a particular embodiment and such terminology shall not be considered to limit the scope of the present disclosure.
The terminology used, in the present disclosure, is only for the purpose of explaining a particular embodiment and such terminology shall not be considered to limit the scope of the present disclosure. As used in the present disclosure, the forms "a,” "an," and "the" may be intended to include the plural forms as well, unless the context clearly suggests otherwise. Thus, for example, reference to a composition containing “a compound” includes a mixture of two or more compounds. It should also be noted that the term “or” is generally employed in its sense including “and/or” unless the content clearly dictates otherwise. The terms "comprises," "comprising," “including,” and “having,” are open ended transitional phrases and therefore specify the presence of stated features, integers, steps, operations, elements, but do not forbid the presence or addition of one or more other features, integers, steps, operations, elements, components, and/or groups thereof. The particular order of steps disclosed in the method and process of the present disclosure is not to be construed as necessarily requiring their performance as described or illustrated. It is also to be understood that additional or alternative steps may be employed.
The terms "comprises," "comprising," “including,” and “having,” are open ended transitional phrases and therefore specify the presence of stated features, integers, steps, operations, elements, but do not forbid the presence or addition of one or more other features, integers, steps, operations, elements, components, and/or groups thereof. The particular order of steps disclosed in the method and process of the present disclosure is not to be construed as necessarily requiring their performance as described or illustrated. It is also to be understood that additional or alternative steps may be employed.
The expression of various quantities in terms of “% w/w” or “%” means the percentage by weight, relative to the weight of the total solution or composition unless otherwise specified.
The term “active ingredient” (a.i.) or “active agent” or “active” used herein refers to that component of the composition responsible for control of pest.
Compound of Formula I, chemically known as 3-(difhioromethyl)-l-methyl-N-(3',4',5'- trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide, is also referred as Fluxapyroxad in the specification.
“Bioactive amounts” as mentioned herein means that amount which, when applied to plant propagation material for seed treatment, is sufficient to give effect in such treatment.
The term “control” means to inhibit the ability of pests to survive, grow, feed and/or reproduce, or to limit the pests related damage or loss in plant propagation material including seeds, seedlings and crop plants.
The term “health of a plant” or “plant health” is defined as a condition of the plant and/or its products. As a result of the improved health; yield, plant vigour, quality and tolerance to abiotic or biotic stress is increased. As a result, the health of a plant is increased even in the absence of pest pressure. Accordingly, in an especially preferred embodiment according to the invention, the health of a plant is increased both in the presence and absence of biotic or abiotic stress factors.
The term "plant propagation material" is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil. These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring. In a particular preferred embodiment, the term propagation material denotes seeds.
This invention relates to compositions for protecting plants, e.g., seeds of such economically important crops. The invention furthermore relates to plant-protecting composition having synergistically enhanced action and to a method of improving the health of plants by applying said composition to the plants or the locus thereof, for example a plant or a plant propagation material, that is infested or liable to be infested by fungi and insect pests.
The composition of present invention has the special advantage of being highly active against diseases in the soil that mostly occur in the early stages of plant development.
In another preferred embodiment of the invention, the yield of the treated plants is significantly improved.
In another preferred embodiment of the invention, the yield of the plants treated according to the method of the invention, is increased synergistically.
The compound of Formula I of present invention (chemically known as 3 -(difluoromethyl)- 1- methyl-N-(3',4',5'-trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide) is a broad-spectrum carboxamide fungicide, used on a large variety of commercial crops. It stunts fungus growth by inhibiting the SQR enzyme. The application of Formula I compound on crops, plants and plant propagation materials interferes with a number of key fungal life functions, including spore germination, germ tube growth and mycelium growth. This compound has been found to show specific efficacy against diseases such as seedling disease, sheath blight, black point, Botrytis gray mold, early blight and powdery mildew. The chemical structure of compound Formula I is provided below:
Figure imgf000018_0001
The compound i.e. 3-(difluoromethyl)-l-methyl-N-(3',4',5'-trifluorobiphenyl-2-yl)-lH-pyrazole- 4-carboxamide shall be referred to as compound of Formula I in the entire specification and shall be meant to refer to this compound which has the IUPAC name and structure as mentioned herein above.
Out of the known strobilurin fungicides, Trifloxystrobin has shown to have better fungal pest control in comparison to other strobilurin fungicides. Trifloxystrobin has IUPAC name: methyl (2E)-(methoxyimino)(2- { [( {( 1 E)- 1 - [3 - (trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)acetate, which belongs to Oximino -acetate class and is classified as Qol-(quinone Outside inhibition) fungicide. Trifloxystrobin is a widely used fungicide. It has a low aqueous solubility, a low volatility and, based on its chemical properties, it would not normally be expected to leach to groundwater. Trifloxystrobin is represented by the following chemical structure:
Figure imgf000018_0002
Trifloxystrobin Neonicotinoid insecticides being broad spectrum insecticides are a class of neuro-active insecticides chemically similar to nicotine. Neonicotinoids are neurotoxins that target the nicotinic acetylcholine receptor acting as agonists. Neonicotinoids also affects the CNS (central nervous system) of the insects as it binds agonistically to the post-synaptic nicotinic acetylcholine receptors that results in the spontaneous discharge of nerve impulses and eventual failure of the neuron to propagate any signal. Although they are effective as contact insecticides, it is the ability of these chemicals to translocate from the soil into leaves as systemic insecticides that has been one of the primary reasons for their popularity. Neonicotinoids are used to protect a variety of vegetables, fruits, and major crops like corn, cotton, potato, rice, etc. against sucking insects like aphids, whiteflies, thrips, leaf- and plant hoppers. Amongst these neonicotinoid insecticides, Thiamethoxam and/or Clothianidin has been shown to have better insecticidal efficacy.
Thiamethoxam is chemically known as 3-[(2-chloro-l,3-thiazol-5-yl)methyl]-5-methyl-N-nitro- l,3,5-oxadiazinan-4-imine. It has the chemical structure as below:
Figure imgf000019_0001
Thiamethoxam
Thiamethoxam is effective against aphids, thrips, beetles, centipedes, millipedes, sawflies, leaf miners, stem borers and termites. Thiamethoxam is mainly used for control against sucking and chewing insects in vegetables, ornamentals, field crops, deciduous fruits, citrus, cotton and rice. It possesses contact and stomach activity. Its systemic properties have resulted in its use against foliar feeding insects via seed treatment, soil application or through irrigation systems. It is also registered for direct foliar application. Clothianidin was first disclosed in EP0375907. Chemically Clothianidin is known as (E)-l-(2- chloro-l,3-thiazol-5-ylmethyl)-3-methyl-2-nitroguanidine (CAS REG No. 210880-92-5). Chemical structure of Clothianidin is as below:
Figure imgf000020_0001
Clothianidin
Clothianidin is even effective for control of Diptera, Coleoptera and Lepidoptera pests and can be applied by a wide variety of treatment methods. In particular, Clothianidin controls sucking and some chewing insects, such as aphids, thrips, and beetles. Clothianidin may be applied to plant leaves, soil, or seeds.
In one embodiment of the present invention, it is provided a synergistic pesticidal composition for seed treatment, comprises (A) compound of Formula I, chemically known as 3- (difhioromethyl)-l-methyl-N-(3',4',5'-trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives; and (B) Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives; and (C) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, esters or derivatives.
In a preferred embodiment of the present invention, the synergistic pesticidal composition for seed treatment, comprises (A) compound of Formula I, chemically known as 3-(difluoromethyl)- l-methyl-N-(3',4',5'-trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives , in the range of 1 to 20% by weight of the composition; and (B) Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives in the range of 0.1 to 10% by weight of the composition; and (C) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, in the range of 10 to 50% by weight of the composition.
Figure imgf000021_0001
In another embodiment of the present invention, there is provided a process for preparation of such synergistic composition, and a method for using such a synergistic composition to control insect pests and fungal diseases affecting plant propagation material.
In accordance with an embodiments of present invention, the composition is useful for effectively controlling the soil borne and/or seed pests, improve the germination rate and also enhances the vigor/yield of the plant.
The synergistic composition of the present invention is particularly suited for the treatment of plant propagation materials, so that materials like seeds has a degree of protection during its germination and growth.
The present invention includes within its scope, all possible salts, esters and derivatives of the active ingredients of the composition.
The seed treatment application of the present synergistic composition may be carried out, e.g. by spraying, foaming, dusting or otherwise covering the seeds before sowing of the seeds and/or before emergence of the plants.
In a more preferred embodiment, the present invention discloses a seed treatment composition which may be formulated as a Flowable concentrate (FS). Flowable concentrates (FS) are suspensions of solid active ingredients in water which are applied to seeds prior to planting. This formulation is currently most popular type of seed treatment as it is water based and safer to apply. Also, since it is a liquid formulation, there are no dust problems and also provided easy clean up post-treatment machinery which is used for broadcasting.
In another embodiment, the present invention provides a method of protecting a plant propagation material, a plant, parts of a plant and/or plant organs that grow at a later point in time against pathogenic damage or pest damage by applying to the plant propagation material a composition of the present invention.
In another embodiment of the present invention, the synergistic pesticidal composition further comprises agrochemically acceptable excipients which are selected from the group comprising of surfactants/dispersing agents, wetting agents , anti-foaming agents, anti-freezing agent, adjuvants, fillers, biocides/anti-microbial agent, thickeners, thickening agents, polymers, colorants, solvents, binders/structuring agents, thickener, buffering agent, fillers, quick coating agent or sticking agents, stabilizers, preservatives, adjuvants and solvents or a combination thereof.
In an embodiment of the present invention, the pesticidal composition controls various pests in field crops, vegetables, oil seed and pulses, horticulture etc.
In yet another embodiment of the present invention suitable targets for seed treatment are various crop seeds, fruit species, vegetables, spices and ornamental seed, cereals, for example corn/maize (sweet and field), durum wheat, bengal gram, soybean, Groundnut, wheat, barley, oats, rye, triticale, bananas, rice, cotton, sunflower, potatoes, pasture, alfalfa, grasses, turf, sorghum, rapeseed, Brassica spp., sugar beet, egg-plants, tomato, lettuce, iceberg lettuce, pepper, cucumber, squash, melon, bean, dry-beans, peas, leek, garlic, onion, cabbage, carrot, tuber such as sugar cane, tobacco, coffee, turf and forage, cruciferous, cucurbits, grapevines, pepper, fodder beet, oil seed rape, pansy, impatiens, petunia and geranium.
The compositions of the present invention provide control of diseases caused by a broad spectrum of fungal plant pathogens in the Basidiomycete, Ascomycete, Oomycete and Deuteromycete classes. The synergistic composition of the present invention are effective against phytopathogenic fungi, especially occurring in plants, including seed borne fungi and belong to the following classes such as those selected from Ascomycetes (e.g. Penicillium, Gaeumannomyces graminis); Basidiomycetes (e.g. the genus Hemileia, Rhizoctonia, Puccinia); Fungi imperfecti (e. g. Botrytis, Helminthosporium, Rhynchosporium, Fusarium, Septoria, Cercospora, Alternaria, Pyricularia and Pseudocercosporella herpotrichoides); Oomycetes (e. g. Phytophthora, Peronospora, Bremia, Pythium, Plasmopara); Zygomycetes (e.g., Rhizopus spp.). The combination of the present invention is especially effective against Alternaria spp., Ascochyta spp., Aspergillus spp., Claviceps purpurea, Cochliobolus spp., Colletotrichum spp., Diplodia maydis, Erysiphe graminis, Fusarium spp. (such as Fusarium culmorum, Fusarium oxysporum, Fusarium solani, Fusarium graminearum and Fusarium moniliforme, Fusarium subglutinans), Gaeumannomyces graminis, Giberella fujikuroi, Giberella zeae, Helminthosporium spp. (such as Helminthosporium graminearum, Helminthosporium oryzae, Helminthosporium solani), Monographella nivalis, Penicillium spp., Puccinia spp., Pyrenophora spp. (such as Pyrenophora graminea), Peronosclerospora spp., Peronspora spp., Phakopsora pachyrhizi, Phythium spp., Phoma spp., Phomopsis spp., Rhizoctonia spp. (such as Rhizoctonia cerealis, Rhizoctonia solani), Septoria spp., Pseudocercosporella spp., Tilletia spp., Rhizopus spp., Thielaviopsis basicola, Typhula spp., Ustilago spp., Sphacelotheca spp. (e.g. Spacelotheca reilliani), Thanatephorus cucumeris, and Verticillium spp.
The present composition may be used to control insect pests such as insects pests from the following orders: Lepidoptera, for example Agrotis ypsilon, Anticarsia gemmatalis, Chilo partellus, Cnaphalocrosis medinalis, Cydia pomonella, Pythium Diaphania nitidalis, , Earias insulana, Elasmopalpus lignosellus, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hyphantria cunea, Hyponomeuta malinellus, Leucoptera coffeella, Leucoptera scitella, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris bras-sicae, Plutella xylostella, Sitotroga cerealella, Sesamia inferans, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni; beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscu-rus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Aphthona euphoridae, Apogonia aerea, Athous haemorrhoidalis, Atomaria linearis, Blasto-phagus piniperda, Blitophaga undata, Brahmina coriacea , Bruchus rufimanus, Bruchus pisorum, Bruchus lends, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Ctenicera ssp., Diabrotica longicornis, Diabrotica semipunctata, Diabrotica punctata Diabrotica speciosa, Diabrotica virgifera, Epila- chna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, White grub species, Holotrichia consanguinea , Holotrichia serrata, Holotrichia longipennis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographic, Lema bilineata, Lema melanopus, Lepidiota stigma, Leptinotarsa decemlineata, Limonius califomicus, Lissorhoptrus oryzophilus, Melanotic communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oberea (Obereopsis) brevis, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllobius pyri, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha hordeola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sito-philus gran aria; flies, (Diptera), e.g. Atherigona orientalis, Atherigona soccata, Athalia lugen proximo, Dacus cucurbi-tae, Dacus oleae, Glossina palpalis, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia platura, Hypoderma lineata, Leptoconops torrens, Leaf miner, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia titillanus, Mayetiola destructor, Oscinella frit, Phorbia brassicae, Prosimulium mixtum, Rhagoletis cerasi, Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, Tipula oleracea, and Tipula paludosa; thrips (Thysanoptera), e.g. Dichromothrips corbetti, Dichromothrips ssp , Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Scirtothrips dorsalis, Thrips oryzae, Thrips palmi and Thrips tabac;, termites (Isoptera), e.g. Calotermes flavicollis, Coptotermes formosanus, Heterotermes aureus, Leucotermes flavipes, Microtermes spp., Odontotermes, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus and Termes natalensis; true bugs (Hemiptera), e.g. Acrostemum hilare, Amrasca biguttula biguttula, Amrasca devastans, Blissus leucopterus, Dysdercus cingulatus, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridu-la, Piesma quadrata, Solubea insularis , Thyanta perditor, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis crassivora, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrtho-siphon pisum, Aulacorthum solani, Bemisia argentifolii, Bemisia tabaci, Brachycaudus cardui, Brachy-caudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus homi, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Ma-crosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzus persicae, Myzus ascalonicus, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mail, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosi-phum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mail, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera aurantiia d, Pileus vitifolii, Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., andArilus critatus, Trialeurodes vaporariorum, Amrasca biguttula, Empoasca spp., Myzus spp., Nephotettix spp., Nilaparvata spp., Pianococcus spp., Pseudococcus spp., Psylla spp., Rhopalosiphum spp., Sitobion spp., Amritodus atkinsoni, Idioscopus spp., ants, bees, wasp;, sawflies (Hymenoptera), e.g. Athalia rosae, Atta cephalotes, Atta capiguara, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Monomorium pha-raonis, Solenopsis geminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xyloni, Pogonomyrmex barbatus, Pogonomyrmex califomicus, Pheidole megacephala, Dasy-mutilla occidentalis, Bombus spp. Vespula squamosa, Paravespula vulgaris, Paraves-pula pennsylvanica, Paravespula germanica, Dolichovespula maculata, Vespa crabro, Polistes rubiginosa, Camponotus floridanus, and Linepithema humile, crickets, grasshoppers, locusts (Orthoptera), e.g. Acheta domestica, Gryllotalpa gryllo-talpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca americana, Schistocerca gregaria, Dociostaurus maroccanus, Tachycines asynamorus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis, Kraussaria angulifera, Calliptamus italicus, Chortoicetes terminifera, and Locustana pardalina, plant parasitic nematodes such as root-knot nematodes, Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica,' cyst nematodes, Globodera rostochiensis, Heterodera avenac, seed gall nematodes, Anguina funesta, Anguina tritici and other Anguina species; stem and foliar nematodes, Aphelenchoides besseyi, sting nematodes, Belonolaimus longicaudatus, white fly and other plant parasitic nematode species.
The composition of present invention is suitable for controlling against many phytophagous insects’ pest’s including; Aphids, Jassid, Thrips, white fly, Mites (including termites), Mealybugs, Scales, Leaf miner, Gall midges, shootfly, stemfly, stemborer, root borer, fruit borer and other sucking pests.
In an especially preferred embodiment of the invention, the yield of the treated plant is increased.
In yet another preferred embodiment of the present invention, the pesticidal composition is formulated as Flowable concentrate for seed treatment (FS).
In yet another embodiment of the present invention, the invention further provides the process for preparation of the said composition wherein, the preferred composition is Flowable concentrate for seed treatment (FS).
In accordance to one embodiment of the invention there is provided synergistic seed treatment composition that is non-phytotoxic and has good stability.
As per another embodiment, the said composition is used to controls seed and soil borne fungal diseases like damping off, root rot, stem rot, pre emergence and post emergence seedling rot and blight caused by Pythium, Phytophthora, Rhizoctonia, Fusarium, Sclerotium, Aspergillus, Verticillium, Puccinia, Ustilago, Alternaria, Cercospora, Penicillium, Macrophomina, fungus. Further, the synergistic composition of the present invention is also useful in controlling soil insects like termites and also gives protection to crop after germination against various insects. Seed treatment can be applied to all types of seeds, including those from which plants genetically transformed to express specialized traits will germinate. Furthermore, such seed treatments with the composition of present invention can further enhance the ability of a plant to better withstand stressful growing conditions. This results in a healthier, more vigorous plant, which can lead to higher yields at harvest time.
Seed treatment with the synergistic composition of present invention are planted, the said composition protects the plants that grow after germination of the seed from damage by pests, and thus improves the growth characteristics of the plant through improved control of pests.
Accordingly, the present disclosure includes a method of protecting plants that grow at a later point in time against damage by pests, which method comprises treating seeds with composition comprising (A) compound of Formula I, chemically known as 3 -(difluoromethyl)- 1 -methyl -N- (3',4',5'-trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives and (B) Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives; and (C) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, esters or derivatives.
In addition to treating seeds, the present disclosure also contemplates the treatment of other plant propagation materials. Thus, the descriptions herein involving seed treatment are also intended to apply equally well to methods, compositions and materials involving the treatment of other plant propagation material with the synergistic composition of present invention.
In various embodiments, the seed treatment can be applied as a thin film (such as a dressing) of the formulation including the active ingredient on a seed, where the original size and/or shape of the seed are recognizable; or as a thick film (such as a coating or pelleting) with many layers of the same or different materials where the original shape and/or size of the seed is no longer recognizable. In further embodiment of the present invention, agrochemically acceptable excipients used in the present invention includes but not limited to the group comprising dispersing agent, wetting agent, anti-foaming agent, anti-freezing agent, adjuvants, fillers, antimicrobial/anti-bacterial agent, thickening agent/thickeners, colouring agents, pigments, dyes and solvents or mixtures thereof. Additional components may also be added to present compositions e.g., protective colloids, adhesives, thixotropic agents, penetration agents, stabilisers, quick coating agents, spreaders, binders, anti-caking agents, stickers.
Examples of dispersing agent used herein include but not limited to polyaryl phenyl ether phosphate, tristyryl phenol ethylated, acrylic copolymer, ethoxylated tristryl phenol Sulphate, naphthalene sulfonic acid, sodium salt condensate with formaldehyde, ethoxylated oleyl cetyl alcohol, polyalkelene glycol ether, ethoxylated fatty alcohol , sodium polymethyl methacrylate, sodium polyacrylate, , sodium lignosulphonate, calcium lignosulphonate, alkylphenol polyoxyethylene ether, polycarboxylate, fatty alcohol polyoxyethylene ether, alcohol polyglycol ether or mixtures thereof and is present in the range of 0.5 -10% by weight of the composition.
Examples of wetting agents used herein include but not limited to tristyrylphenol ethoxylate nonionic emulsifier, mixture of non-ionic surfactants , alkoxylated alcohol, block copolymer, alcohol polyglycol ether, alkyl olefin sulphates, dioctyl sulpho succinate, alkyl naphthalene sulphate, alkyl phenol ethoxylates, tri-styrenated phenol ethoxylate, EO/PO block co-polymers, sodium lauryl sulphate, sodium ligno sulphates or mixtures thereof present in the range of 0.5- 10% by weight of the total composition.
Examples of antifoaming agent used herein include but not limited to silicon emulsion based anti-foam agents, Siloxane polyalkyleneoxide, Polydimethylsiloxane, trisiloxane ethoxylates, silicone oil, silicone compound, C10~C20 saturated fat acid compounds or C8~C10 aliphatic alcohols compound, vegetable oil based antifoam, tallow based fatty acids, polyalkyleneoxide modified polydimethylsiloxane or mixtures thereof and present in the range of 0.01-3% by weight of the total composition. Examples of Anti-freezing agent used herein include but not limited to glycol, propylene glycol, mono ethylene glycol, glycerine, diethylene glycol, sorbitol, urea, mannitol, polyethylene glycol or mixtures thereof and present in the range of 0.1 -20% by weight of the total composition.
Examples of adjuvants used herein include but not limited to silicone ethoxylated oil, polyvinyl pyrrolidon, poly vinyl alcohol, blend of poly terpene resin or mixtures thereof and is present in the range of 0.1 - 10% by weight of the composition.
Fillers used herein include but not limited to silicon dioxide, china-clay, kaolin, starch, bentonite, precipitated silica, fumed silica, talcum powder, lactose, ammonium sulphate, sodium Sulphate, magnesium sulphate, sodium citrate, sodium chloride, potassium chloride or mixtures thereof and present in the range of 0.1-80% by weight of the composition.
Examples of anti-bacterial or anti-microbial agents used herein include but not limited to 1,2- benzisothiazolin-3-one, formaldehyde, sodium benzoate/Sodium o-phenylphenate, 5-chloro-2- methyl-4-isothiazolin-3-one & 2- methyl-4-isothiazolin-3-one, potassium sorbate or mixtures thereof and present in the range of 0.01-1% by weight of the composition.
Thickeners or thickening agents used herein include but not limited to polysaccharides, carboxymethyl cellulose, bentonite clay, aluminium magnesium silicate, hydroxy propyl cellulose, xanthan gum, gum arabic, gaur gum, carbomer, chitosan, precipitated silica or mixtures thereof and present in the range of 0.01- 3% by weight of the composition.
Colouring agent used herein includes dyes or pigments and present in the range of 0.1- 10% by weight of the composition.
Examples of solvents used herein include but not limited to heavy aromatic hydrocarbon, N methyl pyrollidone, Di methyl sulfoxide, N- alcohol, alkyl amide, vegetable oil, mineral oil, aromatic solvents, water. Any of the above mentioned solvent can be used either alone or in combination thereof and present in the range of 0.1-90% by weight of the composition.
Additional components for example quick coating agent or sticking agents used herein include but not limited to polyesters, polyamides, poly- carbonates, polyurea and polyurethanes, acrylate polymers and copolymers, styrene copolymers, butadiene copolymers, polysaccharides such as starch and cellulose derivatives, vinylalcohol, vinylacetate and vinylpyrrolidone polymers and copolymers, polyethers, epoxy, phenolic and melamine resins, polyolefins and define copolymers or mixtures thereof. Examples of preferred polymers are acrylate polymers such as poly(methacrylate), poly(ethyl methacrylate), poly(methylmethacrylate), acrylate copoylmers and styrene-acrylic copolymers as defined herein below, poly(styrenecomaleic anhydride), cellulosic polymers such as ethyl cellulose, cellulose acetate, cellulose acetatebutyrate, acetylated mono, di, and triglycerides, poly(vinylpyrrolidone), vinyl acetate polymers and copolymers, poly(alkylene glycol), styrene butadiene copolymers, poly(orthoesters), alkyd resins, and mixtures of two or more of these. Polymers that are biodegradable are also useful in the present invention. As used herein, a polymer is biodegradable if is not water soluble, but is degraded over a period of several weeks when placed in an application environment. Examples of biodegradable polymers that are useful in the present invention include biodegradable polyesters, starch, polylactic acid starch blends, polylactic acid, poly(lactic acid-glycolic acid) copolymers, polydioxanone, cellulose esters, ethyl cellulose, cellulose acetate butyrate, starch esters, starch esteraliphatic polyester blends, modified corn starch, polycaprolactone, poly (namylmethacry late), wood rosin, polyanhydrides, polyvinylalcohol, polyhydroxybutyratevalerate, biodegradable aliphatic polyesters, and polyhydroxybutyrate or mixtures thereof.
Examples of spreaders used herein include but not limited to organosilicone surfactants, trisiloxane ethoxylate or mixtures thereof.
In an embodiment, the kit-of-parts comprises an instructions manual, said instructions manual comprising instructions directing a user to admix the components before being used.
The process for preparing the present novel synergistic composition can be modified accordingly by any person skilled in the art based on the knowledge of the manufacturing the formulation. However, all such variation and modification is still covered by the scope of present invention.
The composition of the present invention can also comprise or may be applied together and/or sequentially with further active compounds. These further compounds can be selected from fertilizers or micronutrient donors or microorganisms or other preparations that influence plant growth, such as inoculants (e.g. a strain of nitrogen-fixing bacteria), and plant inducers.
Thus, before describing the present invention in detail, it is to be understood that this invention is not limited to particularly exemplified systems or process parameters that may of course, vary. It is also to be understood that the terminology used herein is for the purpose of describing particular embodiments of the invention only and is not intended to limit the scope of the invention in any manner. The use of examples anywhere in this specification including examples of any terms discussed herein is illustrative only, and in no way limits the scope and meaning of the invention or of any exemplified term. Likewise, the invention is not limited to various embodiments given in this specification. Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. In the case of conflict, the present document, including definitions will control.
In order that the present invention may be more readily understood, reference will now be made, by way of example, to the following description. It will be understood that the specification and examples are illustrative but not limitative of the present invention and that other embodiments within the spirit and scope of the invention will suggest themselves to those skilled in the art. Other embodiments can be practiced that are also within the scope of the present invention. The following illustrations of examples are intended to illustrate a stable synergistic fungicidal composition, but in no way limit the scope of the present invention.
A representative example of synergistic pesticidal composition for seed treatment comprising (A) compound of Formula I, chemically known as 3-(difhioromethyl)-l-methyl-N-(3',4',5'- trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, ester or derivatives; and (B) Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives; and (C) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, esters, or derivatives may be provided as follows: Examples
A stable Flowable Concentrate/Slurry (FS) composition of present invention:
Table 1:
Figure imgf000032_0001
Figure imgf000033_0001
Example: 1
Figure imgf000034_0001
Process: Mixture of surfactants & anti-freezing agent (Glycerin) were first diluted in required D.M. Water, and then solubilized by high shear mixing and then added Compound of Formula I, Trifloxystrobin, Clothianidin Technical, defoamer, dye and mixed to make homogeneous mass. The above mixed mass grinded in Bead Mill. Grinding was carried out until a mean particle size of below 5 microns obtained. Preparations of 2% gum solution - Took 100 g DM water added 0.2 g of PROXEL GXL added slowly under stirring and then 2 g xanthan gum added. After the grinding, added 2% water solution of xanthan gum under low stirring. After mixing till homogeneous and check for quality parameter.
Example:!
Figure imgf000035_0001
Stability Data: Trifloxystrobin 4% + Compound of Formula I 6.66% + Clothianidin 25% FS
Figure imgf000035_0002
Figure imgf000036_0001
Figure imgf000037_0001
Examples on Efficacy:
Evaluation of synergistic pesticidal compositions for seed treatment of the present invention
A synergistic effect of two or more products exists whenever the action of an active ingredient combination is greater than the sum of the actions of the individual components. Synergism was calculated by using Colby’s method (Weeds, vol. 15 No. 1 (Jan 1967), pp. 20-2.
The synergistic action expected for a given combination of two active components can be calculated as follows:
XY
E = (X + Y) - -
100
The synergistic action expected for a given combination of three active components can be calculated as follows:
(XY+YZ+XZ) (XYZ)
E = (X + Y + Z) - - + -
100 10000
Where:
E represents expected percentage of pesticidal control for the combination of the two or three active ingredients at defined doses (for example equal to x, y and z, respectively).
X is the percentage of pesticidal control observed by the compound (Fluxapyroxad/ Compound of Formula I ) at a defined dose (equal to x).
Y is the percentage of pesticidal control observed by the compound (Trifloxystrobin) at a defined dose (equal to y). Z is the percentage of pesticidal control observed by the compound (Thiamethoxam or Clothianidin) at a defined dose (equal to z).
When the percentage of pesticidal control observed for the combination is greater than the expected percentage, there is a synergism effect.
Observed control (%)
Ratio = -
Expected control (%)
Ratio of O/E > 1, synergism observed
The present invention is illustrated by way of examples, the examples are meant for illustrative purposes and should not be construed as limiting.
Experiment for Synergistic activity of pesticidal composition for seed treatment of present invention:
Example 1- Details of experiment on ground nut crop:
Field trial had been carried out to evaluate the efficacy of synergistic activity of readymade pesticidal composition for seed treatment of present invention on ground nut crop against different binary and solo formulation.
Location: Bikaner, Rajasthan
Variety: Raj Mungphali-1 (RG-510)
Treatments: For evaluation of synergy of novel pesticidal composition ready mix pesticidal compositions comprising Fluxapyroxad + Trifloxystrobin + Thiamethoxam and Fluxapyroxad + Trifloxystrobin + Clothianidin of present invention in different ratios were evaluated against ready mix of binary formulations and solo formulations at ratios. The treatment details are as under:
Ready Mix Pesticidal Compositions
T1 - Fluxapyroxad + Trifloxystrobin + Thiamethoxam FS (l%+0. l%+50%)
T2 - Fluxapyroxad + Trifloxystrobin + Thiamethoxam FS (6.66%+4.0%+25%) T3 - Fluxapyroxad + Trifloxystrobin + Thiamethoxam FS (20%+10%+10%) T4 - Fluxapyroxad + Trifloxystrobin + Clothianidin FS (l%+0.1 %+50%)
T5 - Fluxapyroxad + Trifloxystrobin + Clothianidin FS (6.66%+4.0%+25%) T6 - Fluxapyroxad + Trifloxystrobin + Clothianidin FS (20%+10%+10%)
Ready Mixes of Binary Formulations
T7 - Fluxapyroxad + Trifloxystrobin FS (l%+0.1%)
T8 - Fluxapyroxad + Trifloxystrobin FS (6.66%+4.0%)
T9 - Fluxapyroxad + Trifloxystrobin FS (20%+10%)
T10 - Fluxapyroxad + Thiamethoxam FS (1 %+50%)
Ti l - Fluxapyroxad + Thiamethoxam FS (6.66%+25%)
T12 - Fluxapyroxad + Thiamethoxam FS (20%+10%)
T13 - Fluxapyroxad + Clothianidin FS (1 %+50%)
T14 - Fluxapyroxad + Clothianidin FS (6.66%+25%)
T15 - Fluxapyroxad + Clothianidin FS (20%+10%)
T16 -Trifloxystrobin + Thiamethoxam FS (0. l%+50%)
T17 -Trifloxystrobin + Thiamethoxam FS (4.0%+25%)
T18 -Trifloxystrobin + Thiamethoxam FS (10%+l 0%)
T19 -Trifloxystrobin + Clothianidin FS (0.1%+50%)
T20 -Trifloxystrobin + Clothianidin FS (4.0%+25%)
T21 -Trifloxystrobin + Clothianidin FS (10%+l 0%)
Solo Formulation
T22 - Fluxapyroxad FS (1%)
T23 - Fluxapyroxad FS (6.66%)
T24 - Fluxapyroxad FS (20%)
T25 - Trifloxystrobin FS (0.1%)
T26 - Trifloxystrobin FS (4.0%)
T27 - Trifloxystrobin FS (10.0%)
T28 - Thiamethoxam FS (50.0%)
T29 - Thiamethoxam FS (25%)
T30 - Thiamethoxam FS (10.0%) T31 - Clothiamdin FS (50.0%)
T32 - Clothiamdin FS (25%)
T33 - Clothiamdin FS (10.0%)
T34 - Untreated check
Dose: 6 ml/kg seed
Replications: Three (3)
Plot Size: 10 m x 10 m (100 sq. m)
Spacing: 45 cm x 10 cm
Seed Rate: 100 kg/ha
Application Method: Required quantity of seeds were treated with different compositions as per treatment schedule using seed slurry method. Treated seeds were placed in shade to dry for 2-3 hrs and then sown.
Date of Application: August 18th, 2022.
Date of Sowing: August 18th, 2022
Method of sowing: Line sowing on flat beds.
Agronomic Management:
1. Nutrient Management: Use of N:P:K @ 75:25:50 kg/ha and micro-nutrients as per requirement.
2. Weed Management: Two hand weeding, first around 20 days after sowing and 2nd at about 40 days after sowing.
3. Water Management: Protective irrigation is given at 5 DAS, 30 DAS (Flowering), 55 DAS (Pod formation) and 80 DAS (Pod filling). Methods of Observations:
Germination Percentage: Counted number of seeds were sown in 10 sq m area in each plot are marked and germination percentage is calculated as given below
Germinated seeds
Germination Percentage (%) = - XI 00
Total no of seeds sown Plant Stand: Total no of healthy plants from 10 sq mts area from 3 different parts of each plot were recorded and converted into per plot.
Collar rot (Aspergillus niger). Total no of infected were counted at 30 days after sowing in each plot and percentage collar rot control was calculated as
Collar rot control (%) Total no of infected plants in treatment X
=
Figure imgf000041_0001
Total no of infected plants in control
Figure imgf000041_0002
100
White Grub: Damage is caused by grubs where, young grubs feed on fine rootlets while mature grubs feed on both roots and pods. The affected plants show varying degrees of wilting, which ultimately die and died plants can easily be pulled out. The grubs cause infestation in patches leading to ‘patchy appearance’ of field. For recording the observation for damage due to white grub total no of wilted/dead plants were counted at 30 days after sowing in each plant and percentage white grub control was calculated as
Total no of wilted/dead plants in
White Grub control treatment \ X
(%) = Total no of wilted/dead plants in 1 100
Figure imgf000041_0003
control '
No. of pods per plant: No. of pods per plants was recorded at the time of harvest. For recording the observation average of 10 plants from each plot were taken. Yield: Pods from each plot were recorded at harvest and converted into kg/ha.
Table 1: Efficacy of pesticidal combination of the present invention (Fluxapyroxad +
Trifloxystrobin + Thiamethoxam) on germination and Plant Stand
Figure imgf000042_0001
Table 2: Efficacy of pesticidal combination of the present invention (Fluxapyroxad + Trifloxystrobin + Clothianidin) on germination and Plant Stand
Figure imgf000042_0002
Figure imgf000043_0001
Effect of novel pesticidal combination of the present invention (Fluxapyroxad + Trifloxystrobin + Thiamethoxam/ Clothianidin) presented in Table 1 and 2 shows that higher germination percentage, better plant stand is observed with seed treatment of ready mix formulation T1-T6 in comparison to binary and solo formulation treatments.
Table 3: Efficacy of pesticidal combination of the present invention (Fluxapyroxad + Trifloxystrobin + Thiamethoxam) on Collar Rot and White Grub Control
Figure imgf000043_0002
Figure imgf000044_0001
O*: Observed Control E*: Expected Control Colby Ratio: O/E
Table 4: Efficacy of pesticidal combination of the present invention (Fluxapyroxad + Trifloxystrobin + Clothianidin) on Collar Rot and White Grub Control
Figure imgf000044_0002
Figure imgf000045_0001
O*: Observed Control E*: Expected Control Colby Ratio: O/E
Similarly, among treatments pesticidal combination of Fluxapyroxad + Trifloxystrobin + Thiamethoxam/ Clothianidin gave better protection against Collar rot and White grub incidence as evident from data in Table 3-4.
Table 5: Efficacy of pesticidal combination of the present invention (Fluxapyroxad +
Trifloxystrobin + Thiamethoxam) on yield attributes
Figure imgf000045_0002
Figure imgf000046_0001
O*: Observed Control E*: Expected Control Colby Ratio: O/E
Table 6: Efficacy of pesticidal combination of the present invention (Fluxapyroxad + Trifloxystrobin + Clothianidin) on yield attributes
Figure imgf000046_0002
Figure imgf000047_0001
O*: Observed Control E*: Expected Control Colby Ratio: O/E
From Table 5 and 6 it is also evident that the treatment also differed w.r.t. to yield wherein higher POD yield was observed in T1-T3. Ternary pesticidal combination of Fluxapyroxad + Trifloxystrobin + Thiamethoxam/ Clothianidin was also found highly synergistic with > 1 Colby’s Ratio for Collar Rot, White Grub, and Pod yield. The binary combination of two fungicides Fluxapyroxad + Trifloxystrobin (T7 to T9), Fluxapyroxad + Thiamethoxam (T10 to T12), Fluxapyroxad + Clothianidin (T13 to T15), Trifloxystrobin + Thiamethoxam (T16 to T18) and Trifloxystrobin + Clothianidin (T19 to T21) are compatible but non-synergistic for the control of target pest and yield attributes as compared to ternary combination of Fluxapyroxad, Trifloxystrobin, Thiamethoxam and Clothianidin.
From the foregoing data, it is evident that the composition of present invention is stable, synergistically efficacious in terms of disease control and improves the germination and yield of the crops.
Thus, from the above, it will be observed that numerous modifications and variations can be effectuated without departing from the true spirit and scope of the novel concepts of the present invention. It is to be understood that no limitations with respect to the specific embodiments illustrated is intended or should be inferred. It should be understood that all such modifications and improvements have been deleted herein for the sake of conciseness and readability but are properly within the scope of the following claims.
It is to be understood that the present invention is susceptible to modifications, changes and adaptations by those skilled in the art. Such modifications, changes, adaptations are intended to be within the scope of the present invention.

Claims

We Claim:
[CLAIM 1]
A synergistic pesticidal composition for seed treatment comprising: a) compound of Formula I, i.e. 3-(difluoromethyl)-l-methyl-N-(3',4',5'- trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives; b) Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives; c) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, esters or derivatives.
[CLAIM 2]
The pesticidal composition as claimed in claim 1, comprising: a) compound of Formula I, i.e. 3-(difhioromethyl)-l-methyl-N-(3',4',5'- trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives , in the range of 1 to 20% by weight of the composition; b) Trifloxystrobin or its agrochemically acceptable salts, esters or its derivatives, in the range of 0.1 to 10% by weight of the composition; and c) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or its agrochemically acceptable salts, esters or its derivatives, in the range of 10 to 50% by weight of the composition.
[CLAIM 3]
The pesticidal composition as claimed in claim 1 to 2, which further comprises one or more agrochemically acceptable excipients.
[CLAIM 4]
The pesticidal composition as claimed in claim 3 wherein the agrochemically acceptable excipients comprise dispersing agent, wetting agent, antifoaming agent, anti-freezing agent, adjuvants, fillers, anti-bacterial agents, thickeners/thickening agents, colouring agents, solvents or mixtures thereof. [CLAIM 5]
The pesticidal composition as claimed in claim 4, wherein the dispersing agent is selected from the group comprising polyarylphenyl ether phosphate, tristyryl phenol ethylated, acrylic copolymer, ethoxylated tristryl phenol Sulphate, naphthalene sulfonic acid, sodium salt condensate with formaldehyde, ethoxylated oleyl cetyl alcohol, polyalkelene glycol ether, ethoxylated fatty alcohol, Sodium polymethyl methacrylate, sodium polyacrylate, sodium lignosulphonate, calcium lignosulphonate, alkylphenol polyoxyethylene ether, polycarboxylate, fatty alcohol polyoxyethylene ether, alcohol polyglycol ether or mixtures thereof and present in the range of 0.
5 -10% by weight of the composition.
[CLAIM 6]
The pesticidal composition as claimed in claim 4, wherein the wetting agent is selected form the group comprising tristyrylphenol ethoxylate non-ionic emulsifier, mixture of non-ionic surfactants, alkoxylated alcohol, block copolymer, alcohol polyglycol ether, alkyl olefin sulphates, dioctyl sulpho succinate, alkyl naphthalene sulphate, alkyl phenol ethoxylates, tri- styrenated phenol ethoxylate, EO/PO block co-polymers, sodium lauryl sulphate, sodium ligno sulphates or mixtures thereof and present in the range of 0.5-10% by weight of the total composition.
[CLAIM 7]
The pesticidal composition as claimed in claim 4, wherein the antifoaming agent is selected from the group comprising silicon emulsion based anti-foam agents, Siloxane polyalkyleneoxide, Polydimethylsiloxane, trisiloxane ethoxylates, silicone oil, silicone compound, C10~C20 saturated fat acid compounds or C8~C10 aliphatic alcohols compound, vegetable oil based antifoam, tallow based fatty acids, polyalkyleneoxide modified polydimethylsiloxane and mixtures thereof and present in the range of 0.01-3% by weight of the composition.
[CLAIM 8]
The synergistic composition as claimed in claim 4, wherein the anti-freezing agent is selected from the group comprising glycol, propylene glycol, mono ethylene glycol, glycerine, diethylene glycol, sorbitol, urea, mannitol, polyethylene glycol or mixtures thereof and present in the range of 0.1-20% by weight of the composition.
[CLAIM 9]
The pesticidal composition as claimed in claim 4, wherein the adjuvants are selected from the group comprising silicone ethoxylated oil, polyvinyl pyrrolidon, poly vinyl alcohol, blend of poly terpene resin or mixtures thereof and present in the range of 0.1 - 10% by weight of the composition.
[CLAIM 10]
The pesticidal composition as claimed in claim 4, wherein the filler is selected from the group comprising silicon dioxide, china-clay, kaolin, starch, bentonite, precipitated silica, fumed silica, talcum powder, lactose, ammonium sulphate, sodium Sulphate, magnesium sulphate, sodium citrate, sodium chloride, potassium chloride and mixtures thereof and present in the range of 0.1- 80% by weight of the composition.
[CLAIM 11]
The pesticidal composition as claimed in claim 4, wherein the antimicrobial or anti-bacterial agent is selected from the group comprising 1,2- benzisothiazolin-3-one, formaldehyde, sodium benzoate/Sodium o-phenylphenate, 5-chloro-2-methyl-4-isothiazolin-3-one & 2- methyl-4- isothiazolin-3-one, potassium sorbate or mixtures thereof and present in the range of 0.01-1% by weight of the composition.
[CLAIM 12]
The pesticidal composition as claimed in claim 4, wherein the thickener/thickening agent is selected from the group comprising polysaccharides, carboxymethyl cellulose, bentonite clay, aluminium magnesium silicate, hydroxy propyl cellulose, xanthan gum, gum arabic, gaur gum, carbomer, chitosan, precipitated silica or mixtures thereof and present in the range of 0.01- 3% by weight of the composition.
[CLAIM 13]
The pesticidal composition as claimed in claim 4, wherein the colouring agent is selected from the group comprising dyes or pigments and present in the range of 0.1- 10% by weight of the composition.
[CLAIM 14]
The pesticidal composition as claimed in claim 4, wherein the solvent is selected from the group comprising heavy aromatic hydrocarbon, N methyl pyrollidone, Di methyl sulfoxide, N- alcohol, alkyl amide, vegetable oil, mineral oil, aromatic solvents, water or mixtures thereof and present in the range of 0.1-90% by weight of the composition.
[CLAIM 15]
The pesticidal composition as claimed in claim 1 or 2, wherein said composition has particle size distribution of D90 less than or equal to 5 microns.
[CLAIM 16]
The pesticidal composition as claimed in claim 1-15, wherein the use of said composition exhibits improvement in plant health, vigour and yield.
[CLAIM 17]
The pesticidal composition as claimed in any one of the claims 1 to 16, wherein the composition is in form of a flowable suspension (FS) concentrate form.
[CLAIM 18]
A kit-of-parts comprising a plurality of components, wherein said plurality of components comprises: a) compound of Formula I i.e. 3-(Difhioromethyl)-l-methyl-N-(3',4',5'- trifluorobiphenyl-2-yl)-lH-pyrazole-4-carboxamide or its agrochemically acceptable salts, esters or derivatives; b) Trifloxystrobin or its agrochemically acceptable salts, esters or derivatives; c) at least one neonicotinoid insecticide selected from Thiamethoxam or Clothianidin or their agrochemically acceptable salts, esters or derivatives.
PCT/IB2023/061791 2022-11-23 2023-11-22 Pesticidal composition for seed treatment WO2024110891A1 (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009098225A2 (en) * 2008-02-05 2009-08-13 Basf Se Pesticidal mixtures
CN103907608A (en) * 2013-01-06 2014-07-09 江苏丰登农药有限公司 Sterilization composition containing fluxapyroxad and trifloxystrobin and its application
CN108605971A (en) * 2016-12-10 2018-10-02 海利尔药业集团股份有限公司 A kind of seed treatment compositions containing trifloxystrobin

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009098225A2 (en) * 2008-02-05 2009-08-13 Basf Se Pesticidal mixtures
CN103907608A (en) * 2013-01-06 2014-07-09 江苏丰登农药有限公司 Sterilization composition containing fluxapyroxad and trifloxystrobin and its application
CN108605971A (en) * 2016-12-10 2018-10-02 海利尔药业集团股份有限公司 A kind of seed treatment compositions containing trifloxystrobin

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